Water → 2-(1-isopropyl-1H-tetrazol-5-yl)-ethanol

Participants

Reaction Steps

Lithium aluminum hydride (2.1 g, 10 mmol) was added slowly to tetrahydrofuran (30 mL) at 0° C. and a mixture of (2-isopropyl-2H-tetrazol-5-yl)-acetic acid ethyl ester and (1-isopropyl-1H-tetrazol-5-yl)-acetic acid ethyl ester (2 g, 10 mmol) in tetrahydrofuran (20 mL) was added under a nitrogen atmosphere. The reaction was allowed to warm to room temperature and stirred for 16 h. After the resulting mixture was cooled at 0° C., water (0.3 mL) was added slowly, and the reaction was stirred for 30 minutes and filtered through a short silica gel column, which was rinsed with ethyl acetate followed by 20% methanol/methylene chloride. The solution was concentrated in vacuo to provide 2-(2-isopropyl-2H-tetrazol-5-yl)-ethanol and 2-(1-isopropyl-1H-tetrazol-5-yl)-ethanol (1.5 g, 95% yield).

Provenance & Evidence